Pilot.com

Pilot is a back-office services company that combines AI-driven bookkeeping software with US-based finance experts to handle accounting, tax, and CFO work for startups and small businesses. Rather than being a self-serve accounting app, Pilot pairs automated transaction categorization and reconciliation with a dedicated bookkeeper who reviews, explains, and closes the books each month, aiming to give founders investor-ready financials without hiring an in-house finance team.

Beyond core bookkeeping, Pilot offers CFO Services for financial modeling, budget-vs-actuals analysis, fundraising and M&A support, and board reporting; Tax services covering federal and state filings for LLCs, partnerships, S-Corps, and C-Corps; R&D Tax Credit claim handling; Outsourced Operations covering payroll, HR, and invoice/bill management; and Stock Administration for startups managing cap tables through Carta or Pulley. Its platform includes an AI Accountant that answers questions about past transactions and cash flow, live financial dashboards, and integrations with the banking, payroll, and payment tools startups already use.

Pilot describes itself as the largest startup and small business accounting firm in the US, working with thousands of companies including names like OpenAI, Lattice, Airtable, and Scale AI in its customer base. For accounting and bookkeeping firms rather than individual businesses, Pilot also offers Meridian, an AI operating system designed to help firms close client books faster so they can focus on growing their practice.

Pilot is best suited for startups and growing small businesses that want bookkeeping handled end-to-end by a mix of software and human experts, rather than businesses looking to manage their own books directly inside a self-serve accounting platform.

Pilot Bookkeeping: Essentials $99/month (up to $100k monthly expenses; AI categorization, reconciliation, monthly close, year-end tax package). Core starts at $0/month billed annually (for $0 in monthly expenses, scaling up with expenses) and adds a dedicated US-based bookkeeper, cash or accrual books, bill management for up to 10 vendor bills/month, custom chart of accounts, and reports by the 10th business day. Custom plans are quoted for businesses needing QuickBooks migration support, full AP/AR, payroll administration, or CFO advisory, with reports by the 6th business day. Pre-revenue startups can request a discount on Core. Tax add-ons (must be purchased with Bookkeeping): Single-Member LLC from $1,000+/year, Partnerships/S-Corps from $2,000+/year, C-Corps from $2,450+/year, with add-on fees for extra state/city filings and foreign accounts. CFO Services: Basic from $1,750/month, Essentials from $3,150/month, Custom from $5,250/month (all billed annually). Outsourced Operations: Starter $750 one-time setup, Essentials from $500/month, Custom quoted. Stock Administration is free for pre-seed founders (up to 5 cap table members) and $399/hour thereafter. R&D Tax Credit service charges 20% of the credit received.